CA2451006C - 1,2,4-trioxolane antimalarials - Google Patents

1,2,4-trioxolane antimalarials Download PDF

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Publication number
CA2451006C
CA2451006C CA2451006A CA2451006A CA2451006C CA 2451006 C CA2451006 C CA 2451006C CA 2451006 A CA2451006 A CA 2451006A CA 2451006 A CA2451006 A CA 2451006A CA 2451006 C CA2451006 C CA 2451006C
Authority
CA
Canada
Prior art keywords
mmol
trioxolane
mhz
nmr
cdc13
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
CA2451006A
Other languages
English (en)
French (fr)
Other versions
CA2451006A1 (en
Inventor
Jonathan L. Vennerstrom
Jacques Chollet
Yuxiang Dong
Hugues Matile
Maniyan Padmanilayam
Yuanqing Tang
William N. Charman
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
MMV Medicines for Malaria Venture
Original Assignee
MMV Medicines for Malaria Venture
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by MMV Medicines for Malaria Venture filed Critical MMV Medicines for Malaria Venture
Publication of CA2451006A1 publication Critical patent/CA2451006A1/en
Application granted granted Critical
Publication of CA2451006C publication Critical patent/CA2451006C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A61P33/06—Antimalarials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • A61P33/12—Schistosomicides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D323/00—Heterocyclic compounds containing more than two oxygen atoms as the only ring hetero atoms
    • C07D323/02—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/10—Spiro-condensed systems
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Dental Preparations (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CA2451006A 2001-06-21 2002-06-21 1,2,4-trioxolane antimalarials Expired - Lifetime CA2451006C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/886,666 2001-06-21
US09/886,666 US6486199B1 (en) 2001-06-21 2001-06-21 Spiro and dispiro 1,2,4-trioxolane antimalarials
PCT/US2002/019767 WO2003000676A1 (en) 2001-06-21 2002-06-21 1,2,4-trioxolane antimalarials

Publications (2)

Publication Number Publication Date
CA2451006A1 CA2451006A1 (en) 2003-01-03
CA2451006C true CA2451006C (en) 2011-08-23

Family

ID=25389491

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2451006A Expired - Lifetime CA2451006C (en) 2001-06-21 2002-06-21 1,2,4-trioxolane antimalarials

Country Status (24)

Country Link
US (1) US6486199B1 (xx)
EP (1) EP1414813B1 (xx)
JP (1) JP4303585B2 (xx)
KR (1) KR100759144B1 (xx)
CN (1) CN1545508B (xx)
AT (1) ATE339411T1 (xx)
AU (1) AU2002327183B2 (xx)
BR (1) BRPI0210549B8 (xx)
CA (1) CA2451006C (xx)
CY (1) CY1106214T1 (xx)
DE (1) DE60214733T8 (xx)
DK (1) DK1414813T3 (xx)
ES (1) ES2271323T3 (xx)
HU (1) HUP0400246A3 (xx)
IL (1) IL159474A0 (xx)
MX (1) MXPA03011915A (xx)
NO (1) NO20035721L (xx)
PL (1) PL226418B1 (xx)
PT (1) PT1414813E (xx)
RU (1) RU2271357C2 (xx)
SI (1) SI1414813T1 (xx)
UA (1) UA78709C2 (xx)
WO (1) WO2003000676A1 (xx)
YU (1) YU100703A (xx)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE536887T1 (de) * 2002-06-06 2011-12-15 Univ Washington Kovalente konjugate zwischen mit artemisinin verwandten endoperoxiden und eisentragenden proteinen und anwendungsverfahren
US7371778B2 (en) * 2002-06-21 2008-05-13 Medicines For Malaria Venture Mmv Spiro and dispiro 1,2,4-trioxolane antimalarials
US20080125441A1 (en) * 2002-06-21 2008-05-29 Medicines For Malaria Venture Mmv Spiro and dispiro 1,2,4-trioxolane antimalarials
US6825230B2 (en) * 2002-06-21 2004-11-30 Medicines For Malaria Venture Mmv Spiro and dispiro 1,2,4-trixolane antimalarials
US6906205B2 (en) * 2002-06-21 2005-06-14 Medicines For Malaria Venture Mmv Spiro and dispiro 1,2,4-trioxolane antimalarials
FR2862304A1 (fr) * 2003-11-14 2005-05-20 Centre Nat Rech Scient Molecules duales racemiques ou achirales contenant un derive peroxydique, leur synthese et leurs applications therapeutiques
EP1789380A1 (de) * 2004-07-23 2007-05-30 Justus-Liebig-Universität Giessen Aminoadamantan-derivate, verfahren zu ihrer herstellung und ihre verwendung
US20060040761A1 (en) * 2004-08-23 2006-02-23 Sam-Kyu Shin Scale mark mat for putting practice
US8067620B2 (en) * 2005-05-04 2011-11-29 Medicines For Malaria Venture Mmv Dispiro 1,2,4-trioxolane antimalarials
CN101272777B (zh) * 2005-05-18 2013-01-30 兰贝克赛实验室有限公司 螺和二螺1,2,4-三氧戊环抗疟药的稳定剂型
WO2007036947A1 (en) * 2005-09-30 2007-04-05 Ipca Laboratories Limited Delayed release anti-malarial composition
DE602006013668D1 (de) 2005-10-04 2010-05-27 Director General Defence Res & Aus gomphostemma niveum isolierte verbindung gegen malaria
US20070231300A1 (en) * 2006-03-28 2007-10-04 Washington, University Of Covalent conjugates between endoperoxides and transferrin and lactoferrin receptor-binding agents
JP2009533368A (ja) 2006-04-11 2009-09-17 ノバルティス アクチエンゲゼルシャフト 有機化合物
US20090306091A1 (en) * 2006-05-17 2009-12-10 Vyas Madhavrao Shingatgeri Antimalarial therapy using a combination of synthetic artemisinin derivative and bisquinoline derivative
US8569519B2 (en) * 2006-05-24 2013-10-29 Ranbaxy Laboratories Limited Process for the preparation of dispiro 1,2,4-trioxolane antimalarials (OZ277)
FR2902100A1 (fr) * 2006-06-13 2007-12-14 Sanofi Aventis Sa Molecules duales contenant un derive peroxydique, leur synthese et leurs applications en therapeutique
GB0619333D0 (en) * 2006-09-30 2006-11-08 Univ Liverpool Dispiro tetraoxane compounds
WO2008046109A2 (en) * 2006-10-13 2008-04-17 University Of Washington Conjugates of artemisinin-related endoperoxides and hydrazone derivatives for the treatment of cancer
FR2924343A1 (fr) * 2007-12-04 2009-06-05 Palumed Sa Nouvelles utilisations therapeutiques de molecules duales contenant un derive peroxydique.
EP2340829B1 (en) * 2008-07-01 2015-08-05 National University Corporation Okayama University Novel antischistosomal agent
US8618096B2 (en) 2008-07-21 2013-12-31 The Regents Of The University Of California Prodrug compositions and methods for using the same in treating cancer and malaria
AU2012282077A1 (en) 2011-07-14 2014-01-30 Sun Pharmaceutical Industries Limited Stable dosage forms of arterolane and piperaquine
WO2015123595A1 (en) 2014-02-14 2015-08-20 The Regents Of The University Of California Cyclic peroxides as prodrugs for selective delivery of agents
WO2016102672A2 (en) * 2014-12-23 2016-06-30 Bergenbio As Pharmaceutically active compounds
RU2601315C1 (ru) * 2015-06-10 2016-11-10 Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук Способ получения пентаоксаспироалканов
US11072594B2 (en) 2017-06-27 2021-07-27 The Regents Of The University Of California Trioxolane agents
CN108424371B (zh) * 2018-01-19 2021-07-16 北京理工大学 2-(4-氨基环己基)-乙酸乙酯的制备方法
US20210386814A1 (en) * 2020-05-20 2021-12-16 Amanuel Tesfazion Methods and compound for the treatment of malaria

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US3621062A (en) 1966-10-25 1971-11-16 Sterling Drug Inc 2-(8-cyclohexyloctanoyl or 7-cyclohexylheptanoyl)-1-naphthol
US3673222A (en) 1969-11-26 1972-06-27 Sydney Archer 2-(8-cyclohexyloctyl or 7-cyclohexylheptyl)-1,4-naphthoquinone and process for preparation and use thereof
US3682991A (en) 1970-10-19 1972-08-08 Sterling Drug Inc 3,3,5-trimethylcyclohexyl-alkyl-carboxylic acids
US4916204A (en) 1987-07-31 1990-04-10 Massachusetts Institute Of Technology Pure polyanhydride from dicarboxylic acid and coupling agent
US4816478A (en) 1987-08-24 1989-03-28 Thornfeldt Carl R Treatment of acquired immunodeficiency syndrome
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US5559145A (en) 1988-06-01 1996-09-24 Oxaco S.A. 1,2,4-trioxane derivatives
US5270344A (en) 1988-06-24 1993-12-14 Stephen Herman Method of treating a systemic disorder using trioxolane and diperoxide compounds
JP2867529B2 (ja) 1990-01-22 1999-03-08 三菱電機株式会社 投写型表示装置
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Also Published As

Publication number Publication date
RU2004101409A (ru) 2005-06-10
PL226418B1 (pl) 2017-07-31
SI1414813T1 (sl) 2006-12-31
BRPI0210549B8 (pt) 2021-05-25
PT1414813E (pt) 2006-12-29
AU2002327183B2 (en) 2006-03-09
HUP0400246A2 (hu) 2004-08-30
KR100759144B1 (ko) 2007-09-14
US6486199B1 (en) 2002-11-26
CN1545508A (zh) 2004-11-10
JP2004535436A (ja) 2004-11-25
NO20035721D0 (no) 2003-12-19
UA78709C2 (en) 2007-04-25
HUP0400246A3 (en) 2009-12-28
YU100703A (xx) 2006-03-03
MXPA03011915A (es) 2004-05-21
ES2271323T3 (es) 2007-04-16
CY1106214T1 (el) 2011-06-08
ATE339411T1 (de) 2006-10-15
NO20035721L (no) 2004-02-23
BR0210549A (pt) 2005-01-11
CN1545508B (zh) 2012-06-06
RU2271357C2 (ru) 2006-03-10
WO2003000676A1 (en) 2003-01-03
BRPI0210549B1 (pt) 2020-11-10
DE60214733T8 (de) 2008-02-21
KR20040030697A (ko) 2004-04-09
PL367158A1 (en) 2005-02-21
EP1414813A1 (en) 2004-05-06
IL159474A0 (en) 2004-06-01
CA2451006A1 (en) 2003-01-03
DK1414813T3 (da) 2007-01-02
EP1414813B1 (en) 2006-09-13
JP4303585B2 (ja) 2009-07-29
DE60214733D1 (de) 2006-10-26
AU2002327183C1 (en) 2003-01-08
DE60214733T2 (de) 2007-09-13

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Effective date: 20220621